5-(2-Bromoethyl)-2,3-dihydro-1-benzofuran → (R)-3-((bis(3-fluorophenyl)methoxy)carbonyl amino)-1-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1910489Notes

Reaction equation

HRID 1910489 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10](=[O:27])[O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH2:2]2.[Br:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]2[O:38][CH2:37][CH2:36][C:35]=2[CH:39]=1>C(OCC)(=O)C>[Br-:28].[F:26][C:22]1[CH:21]=[C:20]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[O:11][C:10]([NH:9][C@@H:3]2[CH:4]3[CH2:7][CH2:8][N+:1]([CH2:29][CH2:30][C:31]4[CH:32]=[CH:33][C:34]5[O:38][CH2:37][CH2:36][C:35]=5[CH:39]=4)([CH2:6][CH2:5]3)[CH2:2]2)=[O:27])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 218311605-(2-Bromoethyl)-2,3-dihydro-1-benzofuranHCID 66575633(R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate

Product 1

HCID 70925754(R)-3-((bis(3-fluorophenyl)methoxy)carbonyl amino)-1-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate (53 mg, 0.14 mmol, prepared as in example 1) in ethyl acetate (2 ml), 5-(2-bromoethyl)-2,3-dihydrobenzofuran (32.3 mg, 0.14 mmol) was added. The resulting mixture was stirred at room temperature for 8 days, and then the solvent was evaporated, and the crude was purified by flash chromatography (DCM/MeOH=95/5) to collect (R)-3-((bis(3-fluorophenyl)-methoxy)carbonylamino)-1-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (22.2 mg).

Workup

  1. customthe solvent was evaporated
  2. customthe crude was purified by flash chromatography (DCM/MeOH=95/5)
  3. customto collect (R)-3-((bis(3-fluorophenyl)-methoxy)carbonylamino)-1-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (22.2 mg)

Sources & evidence

ORD record
ord-142360414b68462f91c807450b41bccc
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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